2-Bromopyridine → 2-(3-Bromophenyl)pyridine

HRID 1897972Notes

Reaction equation

HRID 1897972 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Br:8][C:9]1[CH:10]=[C:11](B(O)O)[CH:12]=[CH:13][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].C(COC)OC>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[Br:8][C:9]1[CH:14]=[C:13]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:12]=[CH:11][CH:10]=1

Participants

8

Reactant 4

HCID 79732-BromopyridineHCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 2734318(3-Bromophenyl)boronic acid

Product 1

HCID 111155062-(3-Bromophenyl)pyridineYield 76%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

2-bromopyridine (75.0 g, 475 mmol), 3-bromophenylboronic acid (104.8 g, 520 mmol), palladium acetate (2.6 g, 2.5 mol %), triphenylphosphine (5.37 g, 5 mol %) and potassium carbonate (196.0 g, 1425 mmol) was placed in a 2 L 3-neck round bottom flask. 500 mL of dimethoxyethane and 500 mL of H2O was added to the flask. Nitrogen was bubbled through the solution for 30 minutes and then the solution was refluxed for 8 h in an atmosphere of nitrogen. The reaction was then allowed to cool to room temperature and the organic phase was separated from the aqueous phase. The aqueous phase was washed with ethylacetate and the organic fractions were combined and dried over magnesium sulfate and the solvent removed under vacuum. The product was chromatographed using silica gel with ethylacetate and hexanes as the eluent. The solvent was removed to give 84.0 g of a clear oil (76% yield).

Workup

  1. customNitrogen was bubbled through the solution for 30 minutes
  2. temperaturethe solution was refluxed for 8 h in an atmosphere of nitrogen
  3. customthe organic phase was separated from the aqueous phase
  4. washThe aqueous phase was washed with ethylacetate
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent removed under vacuum
  7. customThe product was chromatographed
  8. customThe solvent was removed

Sources & evidence

ORD record
ord-d1932e26396447be980dff83405f2e6a
Source dataset
uspto-grants-2013_08
Patent number
US08519384B2

Reaction notes

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